How to Push Your Boss off of Windows Server 2003 and Move to the Cloud

By now, everyone who is remotely connected to the tech world knows that in July Microsoft is planning digital euthanasia for Windows Server 2003. Sure, life support will be available for a while--for a price. But does it really make sense to patch your old server with bubble gum and bailing wire?

To you, the answer may be a loud and hearty “no.” In fact, if your CEO or biggest client is tech-savvy, then you probably upgraded months or even years ago. But what if the guy in the corner office doesn’t quite get it yet? What if he thinks it ain’t broke and doesn’t need fixing?

If that’s the case, here are a handful of nuggets you might find helpful in convincing him or her to make a change:

1. You don’t want to get hacked.

Aging equipment is like your elderly aunt. The older it gets, the easier it is for unscrupulous people to take advantage. It’s not just your money that’s at risk; it’s your customers’ information and your reputation, too. Which is why . . .

2. The Government recommends upgrading.

Seriously. Check out this link. (When you’re Microsoft, it turns out you can get the feds to help you upsell your customer base.) Uncle Sam wants you off the old crap so you don’t accidentally create another gaping hole in America’s cyber defenses. But this alert is just a friendly reminder. If you’re in an industry like health care, law, finance or insurance . . .

3. You could be out of compliance with the law or industry regulations.

There’s an alphabet soup of rules like HIPAA, SOX, FINRA, etc. that address data security. Just having old equipment doesn’t mean you’re automatically out of compliance, but, if you’re breached, it’s probably going to come up--and not in a good way. Luckily, your company has options now because . . .

4. The cloud is much more secure.

Your boss may take comfort in having mail servers in the hall closet, but you know that your data is much safer in hardened data centers with backup power and failover protocols. It may be time to explain that your company is too big or profitable now to operate like a mom-and-pop. But if he doesn’t buy that, then explain that . . .

5. Moving to the cloud will save you money.

Put the blame on Microsoft if you’d like. The company charges an arm and a leg for its merchandise, only to abandon it a decade or so later. Why play that game? Why not pay a small monthly fee and always have the latest software available? It’s a predictable expense and a scalable solution that can grow as your company does. If nothing else works, try peer pressure. After all . . .

6. Your competitors have already made the switch.

It won’t take too much looking to find a rival company that is using the cloud. Unless your CEO still carries a flip phone, he or she isn’t going to want to be seen as the last holdout. It’s tough love, but sometimes it’s the only way.

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